2-(1-((S)-2-mercapto-3-methylbutanamido)cyclopentanecarboxamido)-3-(2'-methoxybiphenyl-4-yl)propanoic acid

ID: ALA2297549

PubChem CID: 76334942

Max Phase: Preclinical

Molecular Formula: C27H34N2O5S

Molecular Weight: 498.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-c1ccc(CC(NC(=O)C2(NC(=O)[C@@H](S)C(C)C)CCCC2)C(=O)O)cc1

Standard InChI:  InChI=1S/C27H34N2O5S/c1-17(2)23(35)24(30)29-27(14-6-7-15-27)26(33)28-21(25(31)32)16-18-10-12-19(13-11-18)20-8-4-5-9-22(20)34-3/h4-5,8-13,17,21,23,35H,6-7,14-16H2,1-3H3,(H,28,33)(H,29,30)(H,31,32)/t21?,23-/m0/s1

Standard InChI Key:  ISGSIHDOIVOYOM-YANBTOMASA-N

Molfile:  

     RDKit          2D

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   13.4003   -8.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8126   -7.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9919   -9.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9190   -6.6421    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8694   -5.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2796   -4.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6291   -4.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0357   -3.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8647   -3.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2706   -3.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0967   -3.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5061   -2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0904   -1.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8556   -2.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5115   -3.7691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1014   -4.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 19 21  1  0
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 13 23  2  0
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 26 25  2  0
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 28 29  2  0
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 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 27 28  1  0
 29 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297549

   3-[4-(2-methoxyphenyl)phenyl]-2-[[1-[[(2S)-3-methyl-2-sulfanylbutanoyl]amino]cyclopentanecarbonyl]amino]propanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 498.65

Molecular Weight (Monoisotopic): 498.2188

AlogP: 3.86

#Rotatable Bonds: 10

Polar Surface Area: 104.73

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.73

CX Basic pKa: ┄

CX LogP: 4.55

CX LogD: 1.25

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -0.17

References

1. Tanneeru K, Sahu I, Guruprasad L.  (2013)  Ligand-based drug design for human endothelin converting enzyme-1 inhibitors,  22  (9): [10.1007/s00044-012-0433-z]

2. Umekawa, K K and 5 more authors.  2000-09  Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme.  [PMID:11043447]

3. Inguimbert, Nicolas N and 6 more authors.  2002-03-28  Toward an optimal joint recognition of the S1' subsites of endothelin converting enzyme-1 (ECE-1), angiotensin converting enzyme (ACE), and neutral endopeptidase (NEP).  [PMID:11906289]

4. Berger, Yann Y and 6 more authors.  2005-01-27  Endothelin-converting enzyme-1 inhibition and growth of human glioblastoma cells.  [PMID:15658862]

5. Seed, Alison A and 8 more authors.  2012-10-15  The dual endothelin converting enzyme/neutral endopeptidase inhibitor SLV-306 (daglutril), inhibits systemic conversion of big endothelin-1 in humans.  [PMID:22480515]

6. McKinnell, R Murray RM and 13 more authors.  2019-01-10  Discovery of TD-0212, an Orally Active Dual Pharmacology AT1 Antagonist and Neprilysin Inhibitor (ARNI).  [PMID:30655952]

Source

Source(1):

• Scientific Literature